To me, the answer to the question of when you should use emoji is an emphatic always. But I get it, if you're texting something important to a humorless prick, a top hat with a lipstick kiss and prayer hands might not be well received. So follow this flowchart created by artist and friend of GizmodoWendy MacNaughton and Caroline Paul to figure out proper emoji etiquette.

I never ever used emoticons before but I'm a sucker for a timely emoji. Hell, I'm a sucker for overusing emojis. That's what they're there for, right? [Tech Page One via Explore]